Hans jobdan



Chemical product and Patented Aug. 7, 1928.

UNITED STATES PATENT OFFICE.

HANS JORDAN, or BEnLm-s'rnem'rz, GERMANY, ASSIGNOR ro run FIRM: onnmsonn mumrx nornc'rmn vomit. n scnnnme, or BERLIN, GERMANY.

- ALKYL CUHABANES AND PROCESS OF MAKII N'G SAME.

No Drawing. Application 11c" .lune 20, 1927, Serial No. 200,291, and in Germany June 29, 1926.

My invention refers to chemical products having valuable properties more especially as solvents for lacquers and the like and as starting materials for the manufacture of thymol and menthol. The new products are obtained by decomposition of those products which result in the condensation, effected at temperatures below 100 C. in thepressure of condensing agents such as hydrochloric acid, bet-ween alkyl phenols and ketones described in my copending application for petent of the Unitedlstates Serial No. 200,289 filed of even date herewith and entitled rocess of making same. These products of condensation contain acylizable hydroxyl groups and probably have the constitution shown for the product from m-cresol following formula and acetone by the CH: I. have now ascertained that if these products of condensation are heated to about-- rial heated to about 300 C. by slight evacuacollected.

tion, the degree of evacuation being chosen in such manner. that the original product does not distil over. The components being Qalkyl isopropylene phenols and cumaranes,

can be separated from each other by fractional distillation and the cumaranes can be Example 1.

The product of condensation from m-cresol and acetone described in my copending application above mentioned, if heated to about 300 (1, is decomposed into its constituents, which distil over. Preferably distillation is expedited by evacuation. On subjecting the distillate to fractionation there is obtained, besides 3-methyl-6-isopropylene phenol, the dimethyl cumarane which boils' under 11 mms. mercury pressure at 98 C. It has the formula C CHI E 'a:ample 2.

\ C. and having the formula v o EwampZeB.

The roduct of condensation from crude cresol, eing a mixture from mand p-cresol and acetone, described in my above mentioned copending application is heatod'to about 300310? 0., when its constituents will distil over and can be separated by fractional distillation, resulting in the recovery, besides of a mixture of 3- and 4-methyl-6- isopropylen phenol, of the two cumaranes described with reference to Examples 1 and 2.

about 300310 C. to-efi'ect decomposition,

subjecting the products of decomposition to fractional distillation, and collecting the alkyl cumaranes. 4

2. The process of producing alkyl cumaranes comprising heating products of condensation of a methyl phenol and acetone to about 300310 C. to effect decomposition," subjecting the products of decomposition to fractional distillation and collecting the methyl culnarane.

3. The process of producingalkyl cumaranesi comprising heating products of condensation of alkyl phenols and a ketone to about 300-310 C. to GHQCtLlQCOHlIJOSitlOIl in Vacuo, subjecting the products of decomposition to fractional distillation, and collecting the alkyl cumaranes.

,4. The process of producing alkyl cunia- 10' I ranes comprising heating products of condensation of crude eresol and acetone to about 300310 C. to effect decomposition, subjecting the products of decomposition to fractional distillation and collecting the di- 15 methyl cumarane.

In testimony whereof I aifix my signature.

HANS JORDAN. 

